Реакция #346354

ord-13912584cd0d47cd8a0335c54d569d09

Уравнение реакции

CC1(C)S[C@@H]2C(NC(=O)Cc3ccccc3)C(=O)N2C1C(=O)OCC(Cl)(Cl)Cl
2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate
CC(=O)O
acetic acid
O=C([O-])[O-].O=C([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+].[Na+]
sodium percarbonate
CC(=O)O
acetic acid
→
CC1(C)C(C(=O)OCC(Cl)(Cl)Cl)N2C(=O)C(NC(=O)Cc3ccccc3)[C@H]2S1=O
2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide

Реактанты

CC1(C)S[C@@H]2C(NC(=O)Cc3ccccc3)C(=O)N2C1C(=O)OCC(Cl)(Cl)Cl
2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate
CC(=O)O
acetic acid
O=C([O-])[O-].O=C([O-])[O-].OO.OO.OO.[Na+].[Na+].[Na+].[Na+]
sodium percarbonate
CC(=O)O
acetic acid

Реагенты

O.O.[Na+].[Na+].[O]=[W](=[O])([O-])[O-]
sodium tungstate dihydrate

Растворители

O
water
O
water

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.ADDITIONwas added
  2. 2
    Температураwhile cooling in an ice bath
  3. 3
    workup.STIRRINGThe mixture was stirred for 3 hours
  4. 4
    ФильтрацияThe precipitate was collected by filtration
  5. 5
    Промывкаwashed with water
  6. 6
    Другоеdried

Методика

2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate (466 mg.) was added to acetic acid (2 cc), and sodium percarbonate (377 mg.) was added thereto while cooling in an ice bath. The mixture was stirred for 30 minutes, and sodium tungstate dihydrate (40 mg.), acetic acid (1 cc) and water (1 cc) were added thereto. The mixture was stirred for 3 hours, and then water (50 cc) was added thereto. The precipitate was collected by filtration, washed with water and dried to yield crude crystals (400 mg.) of 2,2,2-trichloroethyl 6-(2-phenylacetamido)-2,2-dimethylpenam-3-carboxylate-1-oxide, m.p. 165° - 167° C.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04036847uspto-grants-1977_07